Azo dyestuffs



Patented May 29, 1923.

RICHARD STU'SSEB, OF DENTZ, GERMANY, ASSIGNOB TO FARIBENFABBIKEN YORK.

FBIEDB. BAYER AND (70., F LEVERKUSEN, NEAR COLOGNE-ON-THEFBHINE, GEE- MANY.

No Drawing To all whom it may concern:

Be it known that I, RICHARD S'riissER, a citizen of Germany, residing at Dentz, Germany, have invented new and useful Imrovements in Azo Dyestufi's, of which the ollowing is a specification.

According to the present invention new and valuable cotton azodyestufi's are obtained by combining one molecular proportion of the tetrazocompound of the 4.4- diaminodiphenyl-3.3'-dicarboxylic acid having most probably the formula:

OOH

OOH

with one molecular proportion of each of which one contains sulfonic'or carboxylic groups.

- and pulverized in the shape of their alka- 25 line salts dark powders soluble in water and a in concentrated sulfuric acid generally with from a yellow to blue coloration. They yield by reduction with stannous chlorid and hydrochloric acid 4.4 -diaminodiphenyl- 3.3-dicarboxylic acid, an. aromatic amin and an aromatii'gamin contaigiingran acid on e. a su omc or acar oxy 1c rou iii b th. They dye cotton from yell o w t2 orange to violet to blue shades which when aftertreated with copper salts generally change into deeper shades, e. g., from violet to blue, from red to blue-red, from orange to yellowish-brown, etc. The aftertreated shades are distinguished for an excellent fastness to light and to washing.

In orderto illustrate my invention more fully the followingv example is given, the parts being'by weight:

544 parts of 4.4-diaminodiphenyl-3.3- dicarboxylic acid are tetrazotized in glacial acetic acid with 27 6 parts of sodium nitrite and 750 parts of hydrochloric acid 19%; B. To the resulting tetrazo solution 438 parts of phenyl-beta-naphthylamindissolved in glacial acetic acid is added. After the formation of the intermediate product is comlete it is filtered off and stirred into a sontim of 461 parts of 5.5-dioxy-2.2-di- Application filed December 23-, 1921. Serial No. 524,483.

when aftertreated with copper sulfate change into blue shades fast to light and to washing.

In the following table the shades of some of my new dystufi's are given Dyestufi obtained from 4.4-diam'inod'i phenyl-8.8-dicarboxylic acid combined unth:

Alter treated Brownishorange. Brownishbordesux. Violet-blue Green.

Blue.

.. Blue-violet Yellowishbrown.

- Brownishyellow.

Dyes cotton- Methylphenylpyrazolon and l-para-sulfo- Orange...

phenyl-3-methyl-5-pyrazolon. Methyl-z-naphthylamin and l-para-carboxyphenyl-ii-methyl-apyrazolon. Phenyl-Z-naphth lamin and methyl-2- naphthylamin- -sulfonic acid. Aceto-acetic-ortho-chloro-anilid and Mimino- 8-oxynaphthalene-4-sulfonic acid. Phen l-2-naphthyla1nin and LB-aminonap thol-4-su1fonie acid. Phenyl-z-naphthylamin and l-oxynaphtha- 1ene-5-sulfonio acid. Aceto-acetic-ortho-chloro-anilid and W 1- phenyl-5-pyrazolon-3-carboxylic acid. Acetoecetic-anilid and aceto-acetic-anilidpara-carboxylic acid.

Bordeaux I claim 1. The herein described new azodyestufi's, which are after being dried and pulverized in the shape of their alkaline salts dark powders soluble in water and in concentrated sulfuric'acid generally with from a yellow to blue coloration; yielding by reduction with stannous chlorid and hydrochloric acid 4.4 -diaminodiphenyl-3.3' dicarboxylic acid, and two aromatic amines, one and only one of which contains an acid group; dyein cotton from yellow to orange to violet to b ue shades which by an aftertreatment with copper salts generally change into deeper shades fast to light and to washing, substantially as described.

2. The herein described new azodyestufi's, which are after being dried and pulverized in the shape of their alkaline salts dark powders soluble in water and in concentrated sulfuric acid generally with from a yellow to blue coloration; yielding by reduction with stannous chlorid and hydrochloric acid 4.4:-diaminodiphenyl-3.3-dicarboxylic acid, and two aromatic amines,

and in concentrated sulfuric acid with a,

blue coloration; yielding upon reduction with stannous chlorid and hydrochloric acid 4.4-diaminodiphenyl-3.3-dicarboxylic acid, an aminophenyl-naphthylamin and memes 6.6 diamino 5.5 diox 2.2'-dinaphthylamin-7.7-disulfonic aci dyeing cotton violet shades which by an aftertreatment with copper sulfate change into blue shades fast to light and to washing, substantially as described.

4. As new products azodyestuffs such as may be prepared by the hereindescribed process, which comprises combining one molecular proportion of the tetrazo compound of 4.4-diaminodiphenyl-3.3' dicarboxylic acid with one molecular proportion each of two different a-zodyestuffs components,one and only one of which contains an acid group.

In testimony whereof I have hereunto set my hand in the presence of two subscribing wltnesses.

RICHARD sTi'JssER. 

